Production of azodyestuffs on silk



Patented Sept. 10, p r i UNITED STATES PATENT oFFlcE.

KURT WOETZEL, OF KOBE, JAPAN, AND HEINRICH LINE, OF OFFENBACH-ON-THE- MAIN, GERMANY, ASSIGNORS TO I. G. FARBENINDUSTRIE AKTIENGESELLSCHAFT,

OF FRANKFORT, GERMANY.

. PRODUCTION OF AZODYESTUFFS ON SILK.

No Drawing. Application filed November 9, 1925, Serial No. 67,919, and in Germany June 20, 1925.

Our invent-ion relates to the production of The following examples illustrate our inazodyestuifs on natural silk consisting in imvention: 1 pregnating the silk fiber with a solution of an E a l azocomponent having a substantive character and developing with a diazo solution. The bOiled ff ilk 0I cl1appe is impreg- The fabrics, dyed in this manner, also form Hated for about -2 mlnlltes at a part of the present invention witha solution containing 1 gr. of beta-naph- The production of ice colors on natural silk Z of 2-3hydroxy naphtholc acld the is made possible by using azocomponents havllter, then 10 P- of common Salt of the 10 ing a substantive character. As such comwelght f the goods are added and thigoods Pounds the arylides of hydroxynaphthoic are handled for also 20 minutes, centrifuged acids and bodies containing a methylene thoroughly: i d for 10-15 i roup capableof combining may be named, with 9 l Offlla such as for example the diand monoacylacei s 4'mtrof2amsldm m h feebly 15 tylarylides described inwthe Patents acidulated with hydrochloric acid, well Nos. 1,594,864; 1,580,709; 1594,866, and mused a Q for "2 1,594,861 I utes with a nearly bo ling solution, conta1n- The process of producing ice colors on silk of marselues soap m h can be executed by impregnating the boiled rmse m P F l state t passed 30 off silk fiber, preferably at a low temperature by 5 bath contillmng acetlc fqnmc or 5111 (204309 a) and While using a protective COL furic or tartaric acid and dried in a not too loid, with the alkaline 5011mm of the azocomlltwn- The U b .hthalld 9 components having a substantive character f naphtholc acld was lssolved v and by developing with diazo solutions with the T quantity caustic Soda a he surprising result that the quality (if the of 34 after addmon of the double i A tity of Turkey red oil. To the impre 'natin Silk fiber Wlth legard to Stabihty bnghtness bath we then added, as a protective colloid and touch is not affected 1 gr of protectol I double powder p11 a p a 1'1- But the azodyestufis can be produced In the fied cellulose lye, which, as is well-known to 1 335 3? 52x555; g g z gi g g g igthose skilled in the art, will protect silk fibres so boiledoffmd bleached h jf treatiesattire lde after dyemg operatlon' ny undy ed scarlet red shade of an excellent fastness is raw silk or cotton resent and boiled off at the Same time willpnot afiect the dyed Silk obtained. The resulting product may be nor does the latter stain such undyed materepresented by the formula: rials. Q

Finally the impregnation and boiling ofl' N=N of the raw silk may also be executed in the same operation of manufacture and the de- H0 velopment with a diazo solution afterwards. The process may be used also for silk in mixed woven fabrics.

In this manner fast and brilliant dyeings I on silk can be obtained in a simple process of dyeing instead of the hitherto existing expensive and complicated procedures. This result m p could not be foreseen, because beta naphthol Th raw ilk i i t d f about 20 is known to be not adapted for producing ice to 25 minutes at from 25 to 30 C. with a socolors on silk. I lution containing 1.5 gr. of diaceto acetyl- NO: HNO 0 'ortho-tolidin in the liter and developed with a solution containing 1.65 gr. of'diazotised ortho-chloroanilin in the liter, feebly acidulated with hydrochloricacid, well rinsed and then boiled voli' foran hour in a nearly boiling bath, containing 30 p. c. of Marseilles soap, together with undyed raw silk and cotton, then repassed in a second soaping bath containing 10-15 p. c. of Marseilles soap for completely removing the bast and worked up, as described in Example 1. A brilliant yellow is obtained, which neither is diminished in tone by the additional boiling off nor stains the undyed raw silk and cotton, boiled off at the same time. The resulting product may be represented by the formula:

Example 3.

The raw silk is impregnated for about 20-25 minutes at 4060 C. with asolution containing 1 gr. of di-2.3-hydroxy naphthoyl dianisidin in the liter, being boiled otf simuloo m v V U N02 OH H OCH;

(by KURT VVoETzEL) tives of the 2.3-hydroxy naphthoic acid and other bodies containing a methylene group capable of combining and other azo components having a substantive character may be used for impregnating and other diazo compounds for developing. The resulting product may be represented by the formula:

OCH;

OH NO:

NH-C 0 KURT WVOETZEL. HEINRICH LINT.

taneously by the higher temperature of the bath, then the bath is cooled down to 30 C., 10 p. o. of common salt of the weight of the silk are added and the goods are handled for further 20 minutes, centrifuged thoroughly,

7 then developed for 10 minutes with a solution containing 1.75 gr. of diazotised 5-nitro- Q-anisidin in the liter, feebly acidulated with hydrochloric acid, well rinsed and then soaped for half an hour in a nearly boiling bath, containing 15 p. c. of Marseilles soap, for completely developing the color and for completely removing the hast, and worked up as described in Example 1. The used di- 2.3-hydroxy naphthoyl-dianisidin was dissolved with the triple quantity of caustic soda solution of 34 B. and the double quantity of Turkey red oil. I Then such a quantity of caustic soda solution was added to the impregnating bath, that the total quantity was 6 gr. of NaOH in the liter of the impregnating bath. As protective colloid 4.5 gr. of protectol I double powder was added for each liter of the impregnating bath, a beautiful claret of an excellent fastness is obtained. In the same manner other deriva- 

